There are so many incredible regions of Italy to choose from when planning a trip; you could really easily spend a year there and not spend enough time seeing and tasting all that this beautiful country has to offer. While my first choice would be somewhere by the sea (Sicily is still one of my dream trips!) on our last visit to Italy, we traveled for a wedding, and our destination was set for us!
With our home base a villa in Umbria, just on the border of Tuscany, we discovered there were countless day trips we could take: Perugia, Siena, Assisi, Montepulciano, and so many more.
Montepulciano was one of our day trips, and this spectacular medieval city atop a giant hill, surrounded by wine, is well worth a visit, especially during sunflower season in Tuscany. Fields of gold were everywhere! Be prepared to drive and walk some steep streets and alleyways in order to get some of the best views, but be sure to take in the architecture on your way.
We were traveling with a group, which isn’t easy in a town like Montepulciano, but we found some great food nonetheless.
You won’t want to miss the wine cellars of Montepulciano and surrounding areas. I was absolutely fascinated by Contucci.
According to the Contucci website, it’s likely that the Contucci family was living in Montepulciano by the year 1,000. . .
Visiting the cellar is quite the experience. You just keep going down, down, down many flights of stairs to find gigantic wine barrels. An added bonus: on an extremely hot Tuscan day, the cellar is delightfully cold and a break from the baking sun!
We merely got a taste of Montepulciano and would absolutely love to visit again to cover the history, food, wine, and amazing views for longer.
As I mentioned above, the reason for our visit was a wedding, and the location of the ceremony was Cortona, inside its beautiful Cortona Cathedral. Cortona and its surroundings were definite favorites on this trip; I still have one last winery post to write, so stay tuned!
Our final day trip during our week in Italy was to Arezzo. Again, it was a group trip, and finding parking for multiple cars was a bit of a challenge. We actually almost gave up and returned to our villa!
Once we found parking, we didn’t have a ton of time to explore, but we did get to see some great views and cute shops. Truffles are king in the region, and I enjoyed some truffle potato chips while wanting to buy everything in sight. The intoxicating smell of truffles filled the air!
As one does on a hot day in Tuscany, we stopped at a cute patio for refreshments; mine was a cold glass of local white wine with a great view of the surrounding square.
There are definitely lots of moments in Italy where sitting outside enjoying local wine is just all you need.
Arezzo offered beautiful architecture, and while we planned to visit its famous cathedral, our parking issues made us miss opening hours! Perhaps this post is a guide on how NOT to travel?
Instead we enjoyed the great outdoors and explored where the film Life is Beautiful was made.
Even reading about the movie made me cry!
Have you seen it? I think I have watched it at least three or four times, and it is heart wrenching every single time. I actually did not know that Arezzo was the setting of the movie, but it made me love this town even more.
After some shopping and taking in Arezzo’s scenery, we needed to get back to the villa for our final night’s dinner and one last sunset in Umbria.
And that sunset over the vineyards did not disappoint!
A 
